Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde
1998
Résumé
Title serine deriv. I (TBDMS = tert-butyldimethylsilyl; Bn = benzyl) was synthesized from D-serine in excellent overall yield. The reactions of I with Grignard and organocerium reagents were highly stereoselective (Felkin model) to give gamma -hydroxy-beta -amino alcs. II (R = CHMe2, Me, Ph, Bu) in good yield. Transformation of II (R = CHMe2) into (2S,3S)-beta -hydroxyleucine (III) is also reported. [on SciFinder (R)]
Détails
Titre
Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde
Auteur(s)
Laieb, Taoues ; Chastanet, Jacqueline ; Zhu, Jieping
Publié dans
Journal of Organic Chemistry
Volume
63
Numéro
5
Pages
1709-1713
Date
1998
ISSN
0022-3263
Mots-clés (libres)
Alcohols Role: SPN (Synthetic preparation); PREP (Preparation) (amino; hydroxy; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Glycols Role: SPN (Synthetic preparation); PREP (Preparation) (amino; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Asymmetric synthesis and induction (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Addition reaction; Addition reaction (nucleophilic; stereoselective; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); asym synthesis hydroxy amino alc; stereoselective Grignard dibenzylserine aldehyde prepn; organocerium stereoselective addn dibenzylserine aldehyde prepn
Note
CAN 128:154357
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
24184-43-8 (D-Serine methyl ester) Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188802-06-4P; 188802-09-7P; 188802-11-1P; 188802-13-3P; 188802-16-6P; 188840-00-8P; 202478-34-0P; 202478-35-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188839-98-7P; 202478-36-2P; 202478-37-3P; 202478-38-4P Role: SPN (Synthetic preparation), PREP (Preparation) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde)
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
24184-43-8 (D-Serine methyl ester) Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188802-06-4P; 188802-09-7P; 188802-11-1P; 188802-13-3P; 188802-16-6P; 188840-00-8P; 202478-34-0P; 202478-35-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188839-98-7P; 202478-36-2P; 202478-37-3P; 202478-38-4P Role: SPN (Synthetic preparation), PREP (Preparation) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
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Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25